Methanol → HCID 22298443, compound

HRID 1173764Notes

Reaction equation

HRID 1173764 reaction equation
[Cl:1][CH:2]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CO.[H][H]>O>[Cl:1][CH:2]([CH:8]([OH:12])[CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 11424094Ethyl 2-chloro-3-oxohexanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22298443HCID 22298443, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 2-chloro-3-oxohexanoate (2.5 g, 13 mmol), methanol (7.5 ml) and water (0.75 ml) were mixed, and nitrogen substitution was carried out after reducing the pressure. The above catalyst solution was added thereto, and hydrogen substitution (3 atmospheres) was carried out under reduced pressure. The mixture was stirred at 70° C. for 14 hours. After the mixture was cooled to room temperature, the solvent was evaporated away under reduced pressure. The concentrated matter was purified by silica gel column chromatography to obtain the title compound as a colorless oil (1.83 g, yield: 72%) ((2S,3R):(2S,3S):(2R,3S):(2R,3R)=6.2:58.5:33.2:2.2).

Workup

  1. additionThe above catalyst solution was added
  2. temperatureAfter the mixture was cooled to room temperature
  3. customthe solvent was evaporated away under reduced pressure
  4. customThe concentrated matter was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f2a9aadef7a4c1b971c7dc56892c4ea
Source dataset
uspto-grants-2010_11
Patent number
US07834190B2

Reaction notes

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